Chemoenzymatic Dynamic Kinetic Resolution of Primary Benzylic Amines using Pd0 -CalB CLEA as a Biohybrid Catalyst

Karl P J Gustafson; Tamás Görbe; Gonzalo de Gonzalo-Calvo; Ning Yuan; Cynthia L Schreiber; Andrey Shchukarev; Cheuk-Wai Tai; Ingmar Persson; Xiaodong Zou; Jan-E Bäckvall

doi:10.1002/chem.201901418

Chemoenzymatic Dynamic Kinetic Resolution of Primary Benzylic Amines using Pd⁰ -CalB CLEA as a Biohybrid Catalyst

Chemistry. 2019 Jul 11;25(39):9174-9179. doi: 10.1002/chem.201901418. Epub 2019 Jun 24.

Authors

Affiliations

¹ Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91, Stockholm, Sweden.
² Department of Materials and Environmental Chemistry, Stockholm University, 106 91, Stockholm, Sweden.
³ Department of Molecular Sciences, Swedish University of Agricultural Sciences, 750 07, Uppsala, Sweden.
⁴ Department of Chemistry, Umeå University, 901 87, Umeå, Sweden.

PMID: 31050831
DOI: 10.1002/chem.201901418

Abstract

Herein, we report on the use a biohybrid catalyst consisting of palladium nanoparticles immobilized on cross-linked enzyme aggregates of lipase B of Candida antarctica (CalB CLEA) for the dynamic kinetic resolution (DKR) of benzylic amines. A set of amines were demonstrated to undergo an efficient DKR and the recyclability of the catalysts was studied. Extensive efforts to further elucidate the structure of the catalyst are presented.

Keywords: amides; biohybrid catalysts; dynamic kinetic resolution; heterogeneous catalysis; key cross-linked enzyme aggregates.

Grants and funding

2016-03897/Vetenskapsrådet